This dissertation argues that the richness and distinctiveness of modern Yiddish travel literature—with its emphasis on arriving rather than departing—reflects the complexity of such East European Jewish notions as home, homelessness, and wandering. It examines the ways in which the experience of travel affected the search for identity, home, and belonging by Yiddish writers from the first secularized and westernized generation of East European Jews. Yiddish travelogues written in the first four decades of the twentieth century show a curious trend with respect to the search for identity and the destinations that are their subject. These destinations fall into two categories: those with specific Jewish connotations and those without. For writers addressing the latter destination category, even though motivated by the search for a Jewish identity, locales beyond the Jewish map engender the greatest sense of empowerment. Even when their ostensible motivations and emphases are diametrically opposed, they arrive at the same conclusion, that Jews belong simultaneously nowhere and everywhere. Peretz Hirschbein and Melech Ravitch are exemplary illustrations of this tendency: the former laments the countless roads on which Jews have traveled and many borders that separate them; he longs for universal brotherhood and closeness to nature, and as such rejects the diversity of the Jewish experience; the latter, on the contrary, celebrates diversity. How can we explain this trend? It is born of the contradictory set of ideological and artistic aims and interests of a generation that rejected the traditional beliefs and lifestyle of their parents, and that aimed to create a body of modern literature in Yiddish that would equal major European literatures, and that internalized a number of European cultural (primarily literary) tropes. Moreover, this literature was the product of a generation of writers who yearned for an organic connection to Jewish past, present, and future and at the same time saw problems with every existing ideology. The Introduction situates the study within the context of Jewish cultural and literary history and addresses questions of scope and methodology. Chapter 1 analyzes Yiddish travel writers’ fascination with exotic destinations lacking specifically Jewish connotations and its role in these writers’ struggles to define their cultural identity. Chapter 2 analyzes the work of Peretz Hirschbein and argues that his longing for universal brotherhood and closeness to nature reflected both a reluctance to celebrate the diversity of the Jewish experience and an impulse to embrace its global proportions. Chapter 3 focuses on the life and work of Melech Ravitch and contrasts his passion for diversity with the opposite approach of Peretz Hirschbein. Chapter 4 explores Yiddish writers’ travel to Mandate Palestine and to Soviet Russia and focuses on the parallels between travelogues about these two politically charged destinations. Chapter 5 examines the development of Yiddish travel literature after World War II, focusing both on works that describe travel back to Eastern Europe and are dominated by the themes of mourning and preservation, and on later works, filled with the urge to affirm a worldwide Jewish presence. The Conclusion recapitulates the dissertation’s main points and stresses the uniqueness of the Yiddish travelogue and its importance in Jewish studies and beyond.